Her Brother's Keeper (closed)

[StFornicate]

We didn't have a lot of rules, but there was one big rule that was bad news for you if you broke it. No selling to kids. For a lot of us, it was a simple morality issue (in spite of the dubious ethical justifications for our business in the first place!). I'm sure for the guys running the show, it had more to do with a backroom deal struck between our bosses, the Irish mob, and the cops.

My name is Tommy O'Brien, and I'm in charge of the goods in this little section of South Chicago. It's not much, but it's a start, helping my move my way up in the organization. Weed, ecstasy, coke, meth, pills, smack... Whatever comes through this part of town, it's ours.

But anyways, back to what I was saying. We don't sell to kids. There's a big school right smack in the middle of our territory, and it's considered a no-man's land for us. Sometimes, we'll get a new guy in the ranks who just doesn't get it. Johnny Humphrey was one such idiot. We caught him selling weed to middle-school kids, in spite of the initial warning.

We rolled up on him, tossed him in the back of an unmarked van, and dumped him in an abandoned warehouse, bound and gagged.

I didn't bother with a lecture. "Told you not to sell to kids, Johnny," I said, before blowing his face off with my .45. The guys cleaned up and dumped the body in the river late that night, wearing a pair of concrete blocks for shoes.

I had just got done cleaning myself up, in fact, when our group's own little party was getting started. "Yo, Mikey!" I called out. Mikey Newport came rushing in.

"Heya Tommy, what's up?" he asked, nervously. I had to chuckle. I'd been friends with him forever, but he never quite had what it takes to make it with the Organization. Poor guy was ever determined, though, and he needed the money, so I found a few things for him to do every once in a while. Of course, it probably helped his case that he had a smoking hot older sister! She was a part-time model and had a habit of posting teasing-type pics up on her various social media. I definitely kept track of her, and I had a feeling that if Mikey kept coming around, his sister would follow, eventually.
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[Woe_Foe]

http://i461.photobucket.com/albums/qq331/woefoe/c5720152-e26e-43a3-8c14-b188a97a628c_zps5138be22.jpghttp://i461.photobucket.com/albums/qq331/woefoe/b6336f2e-3276-43bd-8017-05137889fa0d_zps276da606.jpg


Name: Lilly Newport
Age: 22
Height: 5'10"
Cup size: 38D

​

It's been about a month since I graduated from Loyola College, having earned my Bachelor's degree in psychology after four years of study. I won't lie, I was pretty much in debt after taking full course loads, buying books and not having worked as I did so. So...when I had trouble finding work after I graduated, my parents took the liberty of inviting me to live back home with them and my little brother. Who was my little brother? Well, his name is Mikey Newport, an eighteen year old now in his senior year of high school. I was protective of my little brother, so when I came up and saw that he behaved and look differently, well, I had a hunch that he was meddling with the wrong type of people. A sister can tell, you know.

Other than worrying for my younger brother, I did some part-time modeling. Okay, maybe modeling was a bit of an overstatement; basically, I took some teasing pictures on Facebook and waited for some comments and likes. I did get a lot of attention though, and it was loads of fun. Yes, I was in a relationship - in fact I was engaged. No, we didn't have sex. Andy (my boyfriend) was a perfect gentleman in that regard and respected my decision to wait. In retrospect, given that he was a police officer, maybe I should have asked him for his input before I did what I did.

Well, I got tired of waiting for Mikey to tell me what was going on - so, when he left to do God knows what, I went right on his computer and thankfully he didn't have a password on. From what I gathered, there was going to be get-together in south Chicago, in a neighborhood that was the complete opposite of ours.

"Jesus Christ, Mikey..." was all I could say, after finding out where he was going today. So, I got in my mother's Sudan and drove there myself...

The place where this 'gang' was meeting was located in some ridiculously shabby neighborhood with some decaying buildings. Everything seemed to fall apart here and judging from these potholes that I was drinking over, I was worried that somehow the road would collapse as well.

I knew that I was going the right way when I saw several cars parked around some shabby block. I parked a block away from the place and got out, dressed in a simple green top, black jeans and running shoes. The wind slightly caressed my long brown hair, which I had tied up to the back of my head in a ponytail.

It was then, when I was near the front door, that I noticed someone familiar. No, it wasn't Mikey, it was...

"Tom, is that you?" I asked as I approached him.

 

[StFornicate]

I had sent Mikey on a little trip to fetch some more booze for our party from one of our houses. Tonight was supposed to be a bit of a celebration, as we'd made significant profits over the past quarter and the bosses were happy, so life was good.

We had a couple guys keeping watch over the party, and I got a text message on my phone when an unknown car had parked nearby, along with a picture of the girl who had gotten out. I smirked as I looked at it, recognizing Mikey's sister Lilly very quickly. I nodded to my buddy Kevin, and he understood immediately what I meant.

We had security protocols, after all. I may be the boss, but nobody outside our crew knew that. Not even Mikey knew that. When outsiders were around, which was quite frequently, especially at gatherings like this, Kevin was "the Boss". He was in reality a highly trusted lieutenant, willing to take the heat for me should it come down.

I made my way out to the front porch; the party inside was filled with smoke and drink, music, dancing girls... Everything a guy could want, really, except that the one thing I really wanted was walking up to the house right at that moment.

"Lilly? Hey! Yeah, it's me all right!" I said, making my way down the steps towards her, stopping her in the front yard. "If you're looking for Mikey, he's not here right now. But he should be back soon."

 

[Woe_Foe]

"Lilly? Hey! Yeah, it's me all right!" he called me back, walking towards me until we were face to face. It was nice to see someone I actually knew around these parts and for that reason alone, made me feel so much safer.

"If you're looking for Mikey, he's not here right now. But he should be back soon."

Tom seemed pretty friendly, which seemed just about right, given the way that I've seen him behave before. I couldn't help but smile when he did so, but quickly I realized just why I was here for. "Yeah, about Mikey. Um...Tom, I really don't think my brother should stick around here. I'm not sure why you're here though, but that's your business. I'd really appreciate it if you could help me get my brother out of this mess though..." I said a bit nervously and judged his reaction.

 

[StFornicate]

I listened to her request, and sidled up next to her. I slid my arm around her, behind her waist, and leaned in close to her.

"You know, Mikey's just been a huge help around here for us. We'd really hate to lose him, he's such a good kid and he seems to have a lot of potential," I replied. I looked up at the porch; most of the guys were inside, but at least one of my guys was over in the darkness smoking a cigarette, keeping an eye on me. I gave him a nod, and he headed inside.

"And you know, Mikey came to us looking for work, as I recall."

 

[Woe_Foe]

Tom's arm snaked its way around my waist, pulling me closer to him as we chatted some more.

"You know, Mikey's just been a huge help around here for us. We'd really hate to lose him, he's such a good kid and he seems to have a lot of potential,"

"Yes, but his potential can be better used elsewhere, don't you think? Come on Tom, you're friends with him, you know that Mikey isn't cut out for this..."

I eyed our surroundings carefully and seeing how suspicious most of these guys were, I actually leaned a bit closer to Tom. Maybe they wouldn't bother me if they thought of us both as an item or something...

"And you know, Mikey came to us looking for work, as I recall."

We walked inside and I continued to talk to Tom, replying with "I know, but it isn't his fault. He's just a little confused of what to do with himself? Please Tom, you've got to help him out..."

 

[StFornicate]

As I guided Lilly inside, I listened to her. She was clearly here to help her brother out, this much was obvious. She didn't want him involved with all this, and who could blame her? It was a dangerous life.

Inside the house, there was smoke and drinks everywhere, and the music was loud. I held Lilly close to me, as the guys tended to be hawks, swooping on any girl they could, but they saw she was with me and steered clear. I nodded to Kevin as we passed him by; he was getting a lap dance from a half naked girl.

"That's the boss," I said in her ear, "but I can help you help Mikey, okay?" I said.

"But first, let's get you a drink," I said, as we found ourselves in the kitchen.

 

[Woe_Foe]

I coughed a bit as we entered, seeing as second-hand smoke quickly enveloped the air quality here. I just nearly ended up covering up my ears with my hands; the bass and treble of the stereo system just had to be on maximum volume, essentially killing off the eardrums of everyone in this room, if I had to take a guess. My eyes instantly went to some man getting a lap dance by some poor woman, dressed in the skimpiest outfit you could possibly imagine. Just why do people choose this lifestyle for themselves?

"That's the boss" I heard Tom whisper into my ear, his lips just nearly touching my earlobe (whether it was done on purpose or not, I had no idea) "but I can help you help Mikey, okay?"

I nodded and mouthed "Thank you", seeing as my words must have been inaudible due to the music. But I did hear:

"But first, let's get you a drink,"

"A-Are you sure?" I asked loudly now, trying to make my voice heard "I don't drink!"

 

[StFornicate]

I winked at her, ignoring her statement about not drinking as I threw some alcohol together in a mixing cup with some ice and shook it up. I'd made this drink plenty of times, and it always did the trick.

It was strong enough for a man, but made for a woman, after all.

The drink came out a bright cherry red color, and tasted like candy. I handed her the glass. I cracked open a beer for myself, and lit a cigarette. "Drink up," I said to her.

 

[Woe_Foe]

I nervously watched as he made the drink, seeing as I absolutely did not want any of that in my system. I tried to say "it's okay" a few more times, but either the music drowned me out or he was very insistent. Either way, I got my red glass of...whatever it was.

"Drink up"

I took a few modest sips of the drink and immediately felt the war sensation go down my throat. So this was booze huh? Well, at least this drink tasted like candy. I wasn't going to gulp it down like some of these people though...

"It's good. Thanks!" I said, trying to get him to hear me.

 

[StFornicate]

"Of course," I replied, and took a drink from my beer. I looked out the door at the party going on; it was loud and we could barely hear each other speak. There was a door out to the back yard. I filled up her cup with what remained in the mixing glass, and then guided her out the back door. The back yard was dark; I flipped the switch but the lightbulb was burnt out.

I turned to her and took a drag on my cigarette.

"So, if I do this favor for you, what are you gonna do for me?" I asked Lilly, my gaze lingering on her sexy body as we stood there facing each other on the back patio. "Your brother's a good worker. The boss will be reluctant to let him go. I guess it's a good thing he doesn't know too much yet," I said.

 

[Woe_Foe]

I suppose that the loudness of the music was even bothering Tom, as he began to lead us out of the crowd for the moment. At least, he did so after refilling my glass...

We ended up in the backyard and it seemed, even through this darkness, to be every bit of run down as the reason of the neighborhood. I turned away from Tom, just as he lit up his cigarette. God, I couldn't stand tobacco.

"So, if I do this favor for you, what are you gonna do for me?"

He got my attention with that, and immediately I turned to face him again "Do for you?"

"Your brother's a good worker. The boss will be reluctant to let him go. I guess it's a good thing he doesn't know too much yet,"

I was stumped. I have no idea what exactly I could offer him to get my brother out of this mess. "I...don't really know. Would I have to work here to help him out?" I said, my right hand holding my nearly full glass of alcohol. "What can I do Tom?"

 

[StFornicate]

I smirked and took a drag on my cigarette. "Tell you what," I said, thinking about all the ways I could take advantage of this situation... "I'll tell Mikey to get the fuck out of here, but you're gonna party with me all night, got it? We're gonna have a good old time about things," I said. I looked her up and down, my gaze lingering on her sensual hourglass form.

"And trust, if you piss me off, I'll have a job for Mikey first thing in morning."

I pulled a joint out and sparked it up...

 

[Woe_Foe]

"Tell you what, I'll tell Mikey to get the fuck out of here, but you're gonna party with me all night, got it? We're gonna have a good old time about things,"

"Oh really? Thank you Tom!" I said really gratefully. I was about to give him a hug, but seeing as he pulled out a joint, maybe it could wait. I didn't need that smell on me. I hated drugs...

"And trust, if you piss me off, I'll have a job for Mikey first thing in morning."

"Deal! Thanks again Tom! You're an angel!" I said, sipping through my glass once again.

 

[StFornicate]

I smiled at her. "I do my best," I said, puffing on the joint as I watch her sip at her drink, a bit too slowly for my taste.

"C'mon now, drink up. Gotta have a good buzz going if you want to party right," I said, taking a deep hit off the joint and holding it in, the weed giving me a nice little high for the moment.

 

[Woe_Foe]

"C'mon now, drink up. Gotta have a good buzz going if you want to party right,"
"Okay okay...um...just give me a second." I said, holding my breath, as if that was going to stop the alcohol from burning in my throat. I wasn't used to the sensation, so it was pretty unpleasant for me. Still, I drank down my glass and grinned, almost as if I accomplished a feat for doing that.

Maybe the alcohol was already having an effect on me, because I could hardly even notice the smell of the joint Tom was smoking. Huh.

"So, what do you want to do?" I asked, eagerly. Maybe a party would do me good?

 

[StFornicate]

"Well, first thing we gotta do is smoke the rest of this joint," I said, smiling deviously at her. This was going to be far too much fun. I'd been lusting after this girl for quite some time now, and it seems that the perfect opportunity to have my way with her has fallen right into my lap. And she seemed for too eager and willing...

I stuck my hand out towards her, offering her the smoking joint. "Just suck in on it and hold it in your lungs for as long as you can," I said, holding it so she could just put her lips right on it and suck.

 

[Woe_Foe]

"Well, first thing we gotta do is smoke the rest of this joint,"

Oh great. Was he serious? One careful look to his facial expression told me that he was and I sudden realized that this 'party' wouldn't be so happy-go-lucky as I thought. I nearly sighed but figured that if I did, that I'd seem pretty uptight. Okay...just this once...

I put my empty glass on a beat up table and brought my fingers closer to that joint.

"Just suck in on it and hold it in your lungs for as long as you can,"

"Um...okay." I answered timidly, bringing the joint to my mouth and sucked on it. A muffled cough nearly escaped my lips, as the smoke was a bit much for me (along with the smell). I held it to my lungs for a bit, before letting it out. God, how was this supposed to be relaxing?

"Like that?" I finally said, hoping that we could put this thing away.

 

[StFornicate]

I watched her puff on the joint, and nearly cough, but she seemed determined to do whatever was necessary to help her brother. Shame I had no intention of letting Mikey go, but she certainly didn't need to know that!

I took the joint back and puffed on it, filling my lungs with the sickly sweet smoke. We still had about half of it to smoke yet, so I handed it back to her.

"Just like that, doll," I said, sidling up next to her, quite close, snaking an arm around behind her, my hand resting on her hip. "But we gotta finish it. No sense in wasting good weed," I said, giving her a wink and a devious smile.

 

[Woe_Foe]

"Just like that, doll,"
"O-Okay..."

It was tough smoking this. Well, it should be understandable to anyone who has never smoked anything before. It felt harsh on my lungs but even so, I took a few more puffs and might have coughed a few times. It was getting a bit easier with every try mind you, but still...

Hell, while I was smoking I didn't even notice that Tom snaked his arm around me again, only this time his fingers were on the bare skin between my jeans and my top.

"But we gotta finish it. No sense in wasting good weed,"

"Yeah, okay." I said, adding "It isn't so bad"

Okay, I lied about it not being so bad.

 

[StFornicate]

Watching her smoke it, I had to stifle a chuckle. It was clear she wasn't a smokee at all, from the way she coughed, but she was so eager and willing to do whatever it took to help her brother...

This was almost too easy.

The joint ran out after I puffed on it once more, and, feeling a nice buzz from it, led Lilly back inside. "Let's get you another drink, huh, wash that smoke out of your mouth," I said, and quickly fixed her another one of the potent candy-tasting mixes. I handed it to her and stepped back, looking her up and down, taking in her luscious curves.

"One more thing, for now," I said. "If you really are gonna party with me, you gotta look the part." I smirked. A goodly amount of her cleavage on display would be nice. "Hey, Alyssa!" I called out, and a moment later another girl, a blonde about Lilly's size, came into the kitchen.

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"Yeah Tommy, what's up?" she asked, eyeing Lilly like a hawk. "She's new."

"Yeah, well, she's gonna party with us tonight, but she needs a better outfit to help her fit in. Why don't you take her upstairs and fix her up with something a little more appropriate for our gathering."

I pulled a little baggie of coke from my pocket and handed it to her. "And have some fun, huh?" I smirked.

 

[Woe_Foe]

"Let's get you another drink, huh, wash that smoke out of your mouth,"
"Sure, that sounds good..."

Okay, I didn't like alcohol either, but it was the lesser of two evils at this point. Besides, I really did need to wash the taste of that joint out with something; might as well be a drink at the bar. Tom was gracious enough then to mix me another, only this time I was much more eager to drink it down. Almost so eager, that I barely noticed Tom checking me out for a moment.

"One more thing, for now,"
"Hm?" I said, finishing my drink.
"If you really are gonna party with me, you gotta look the part."
"How?"

"Hey, Alyssa!" Tom then called out, and some blonde showed up. I can't say that her outfit screamed professionalism; she was dressed in pretty skimpy clothing. He greeted Tom, before looking right at me. Jeez, almost as if I did something wrong.

"Yeah, well, she's gonna party with us tonight, but she needs a better outfit to help her fit in. Why don't you take her upstairs and fix her up with something a little more appropriate for our gathering."

Oh god, he was serious about that? Just what was I going to change in? Nothing too skimpy, I hoped and...did Tom just give her coke?

Before I knew it, I was being dragged upstairs. Oh great. Alyssa seemed too eager to run this errant...

 

[StFornicate]

"C'mon sweetheart, you heard the man," Alyssa said, taking Lilly by the hand and guiding her quickly through a door, down a dark hallway and up a flight of rickety stairs. There was a single lightbulb hanging from a cord at the top of the stairway, barely illuminating their way.

Alyssa led her into a dingy bedroom and flipped on the light switch. A lamp hesitantly flickered to life. The bed sat on the floor had no sheets on it, and the only other furniture was a dresser (which was missing two of its drawers). There was a suitcase filled with women's clothes and accessories sitting on the bed.

Alyssa went over to the suitcase and started pulling out some outfits, before finding a couple and turning back to Lilly. She smirked at her as she looked her up and down.

"You look nervous," Alyssa said simply. "Don't be. It's not everyday Tom takes a shine to a new girl," she said. "Though you seem like too nice of a girl to be running with this crowd. What do you think?" She held up a dress in one hand and a skirt and top in the other. "They should be your size. Looks like you got bigger tits than me, though, so they might be a little tight up top, but I know Tom won't complain."

 

[Woe_Foe]

"C'mon sweetheart, you heard the man,"

It seemed to me that Tom had some pull here; which was strange, given the fact that he was only supposed to be working here like Mikey, right? I followed Alyssa through the crummy place, eventually reaching some dark bedroom with hardly anything in it. The woman pulled out a few outfits, but showing me them both. One dress and one top with a matching skirt.

"You look nervous. Don't be. It's not everyday Tom takes a shine to a new girl. Though you seem like too nice of a girl to be running with this crowd. What do you think?"

She held both outfits and explained further:

"They should be your size. Looks like you got bigger tits than me, though, so they might be a little tight up top, but I know Tom won't complain."

I chuckled a bit before thinking...

"Well, I don't know...I think that I'll take the top and the skirt, if you don't mind. Looks like something that I'd normally wear."

 

[StFornicate]

Alyssa nodded and handed Lilly the outfit. Lilly then immediately went over to the sparse dresser; there was a small handheld mirror laying on top. She dumped the baggie of coke out, pulled out a credit card and started cutting up the fine white powder into lines.

A moment later she had a straw up her nose and was snorting one of the lines. Alyssa sniffed a few times afterward, her breathing heavy and rushed as the drug hit her. "Ho, fuck, that shit's good," she said, turning back to Lilly.

"You gotta try this stuff," Alyssa said, eyeing Lilly with amusement. While the outfit seemed like something Lilly might normally wear, it was probably a size or two smaller than what she would normally wear. The skirt would barely cover her curvaceous ass, and the top was low-cut, showing ample cleavage, and skin-tight; with her bra on, it bunched funny and looked wrong. "You're gonna have to ditch the bra," Alyssa said with a smirk. "That top has one built in, anyway, for a little lift," she said, winking and watching the new girl.